Lillian Cornish kept a detailed record of her 115-day trip traversing the world in 1968.

She had been “frightened to death over the thought of 22 hops over the major oceans of the world,” but planned an itinerary that took her to the United Kingdom, Ireland, Western Europe, Lebanon, Egypt, India, Thailand, Hong Kong, Japan and Hawaii.

She was 60 years old and, for the most part, alone.

Cornish chronicled nearly fainting in the sweltering air of an Egyptian pyramid, and her guide offering “air conditioner” — his skirt’s fabric, to be used as a fan.

She detailed purchasing a slide projector in Hong Kong.

She wrote with dismay of the “thimble”-like coffee cups, and with “admiration” of those who “can drink that strong black thick liquid”: She required cream, which was nowhere to be found.

In her edited and type-written retelling, Cornish apologetically forewarned, “If I’ve said anything offensive, remember that one’s impressions of a place depend upon so many things…”

Kaitlyn Semple was 12 years old when she first read her great-grandmother’s travel diary. Cornish’s stories and photo-slides inspired Semple’s newest project, an atmospheric cabaret called Try Your Wings, which she presents Friday in Regina.

Not quite a musical, not quite a play, it’s simply “stories that weave songs together,” said Semple. The soundtrack comprises songs of Blossom Dearie, a jazz pianist and vocalist from New York whose career took off in the 1950s.

“I’ve definitely noticed that every artist has a legacy project, and this is mine,” said Semple, who began conceiving of this project five years ago.

“I think writing stories about our family is important and usually where we start from,” added Semple. “And it’s a tricky but important thing. Because there’s sometimes in these passages that I’m like, ‘Ooh, that’s juicy and dramatic.’ But then I think about what Lillian would want to be shared. … like, oh, maybe that’s a bit too personal.”

As Semple recounts her mother’s-father’s-mother’s memories, she’ll do so in a 1960s classroom-style setting, since Cornish was a Grade 8 teacher at Massey School. Rebecca Donison designed the set.

In between posing as Cornish’s educator colleagues, they’ll back up Semple in performing Dearie’s music.

Dearie’s best-known songs include “Peel Me A Grape,” “I’m Hip,” and “Unpack Your Adjectives” (the latter written by George Newall for Schoolhouse Rock in 1974). If those titles don’t ring a bell, Semple says to imagine “happy jazz harmony singing.”

“She has this girlish kind of voice; she’s the killer jazz piano player,” said Semple.

Projections of Cornish’s photos, created by videographer Ian Campbell, will add to the atmosphere. Smoke likely won’t.

Cornish “smoked so much. I remember her being very smoky,” said Semple, who visited her great-grandmother at Pioneer Village in her later years. “Greg and I’ve been debating if I should smoke in the show or not, because that was just always her thing. And she says in her travel diary, ‘guess I smoke too much.’ But everyone did in the ’60s.”

During those visits, Cornish introduced her great-granddaughter to Fred Astaire, Ginger Rogers and Gene Kelly.

“I can kind of blame her for getting me into musical theatre,” said Semple.